If in a small work area with a workbench or work table, I like my boxes to go to the ceiling or stack as tall as possible to save space. The box only acts as tool storage. Not as work surface.
Hell, I even use a step stool to get into one top box.
Small footprrint that way and saves precious real estate.
And small footprint means more room for tools if going tall or more room to work in and around if small. Win-win.
If a big shop, if you have several local work benches/tables strategically placed, then small bottom or small stacked roll cab , and go as you can. (40/44" tends to be my max for that) That's where a service cart is also helpful.
Large shop and need to move around ALOT and work at it to do heavy tasks, then bigger roll cab with work surface and vice and it becomes both box and work surface.
Again, it's all a matter of how your workspace is designed and the work surfaces available as well as how often your box or equipment needs to be moved or is even just a temp. work area in itself.
Lots of variables.
No easy answers.
Good luck.